New Synthesis for the Monobactam Antibiotic—LYS228
- 15 May 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (11), 6854-6861
- https://doi.org/10.1021/acs.joc.9b01916
Abstract
A new synthesis of LYS228, fitting for further process development for commercial manufacture is described. The key features of the synthesis include development of new protocols for acylation reactions, application of an asymmetric hydrogenation via dynamic kinetic resolution and a late-stage ring closure to form β-lactam 1.Keywords
Funding Information
- Novartis
This publication has 22 references indexed in Scilit:
- Process Development for the Synthesis of a Monobactam Antibiotic—LYS228Organic Process Research & Development, 2020
- Optimization of novel monobactams with activity against carbapenem-resistant Enterobacteriaceae – Identification of LYS228Bioorganic & Medicinal Chemistry Letters, 2018
- Epidemiological Expansion, Structural Studies, and Clinical Challenges of New β-Lactamases from Gram-Negative BacteriaAnnual Review of Microbiology, 2011
- Has the era of untreatable infections arrived?Journal of Antimicrobial Chemotherapy, 2009
- Dynamic kinetic resolution: an efficient route to anti α-amino-β-hydroxy esters via Ru-SYNPHOS®catalyzed hydrogenationChemical Communications, 2004
- Stereoselective hydrogenation via dynamic kinetic resolutionJournal of the American Chemical Society, 1989
- A novel synthesis of the monobactam antibiotic carumonamThe Journal of Organic Chemistry, 1988
- Hydroxamate approach to the synthesis of .beta.-lactam antibioticsAccounts of Chemical Research, 1986
- Clavalanine (Ro 22-5417), a new clavam antibiotic from Streptomyces clavuligerus. 4. A stereorational synthesisThe Journal of Organic Chemistry, 1985
- Monobactams. Stereospecific synthesis of (S)-3-amino-2-oxoazetidine-1-sulfonic acidsThe Journal of Organic Chemistry, 1982